Many people find that writing a first draft requires much more discipline than rewriting a first draft. It's hard to sit yourself down, think through half-formed ideas from scratch, and not get distracted by more fun things.
That's why I recommend writing a terrible first draft as quickly as you can. Your goal is to speedrun—to blast through the laziness and the blockers to get garbage onto paper. This shortcuts you directly to the rewriting phase, which most people find much less painful.
It's strange how well this works.
This is why, in my bad first draft, I use placeholders any time I'm stuck: when an idea requires more thought than I want to put in, I just write <to fill out> and move on. My goal is to generate and connect ideas. Not to explain everything, and certainly not to say things well. Save that for future drafts.
To repeat, my first draft is just for generating and connecting ideas.
When you write a first draft, you write it for yourself. When you rewrite it, you write it for everyone else.
Supporting points typically come first and resulting points typically come last. But, there is no correct outline. Hundreds of paths lead to your objective.
Here’s an example outline for the objective of Challenging the status quo:
Under each talking point in an outline, I start by writing partially-formed thoughts.
It’s more efficient to speedrun through a bad first draft and improve it later than to try starting from completion.
It’s normal if few ideas come to mind immediately. You’ll discover that the majority of your ideas arrive while writing—not before. You write in order to think.
Later, you'll discover the rest of your ideas by resting and reflecting on what you’ve written. The act of writing compels your brain to draw connections between ideas.
It can’t help itself.
In general, you'll find ideas bubbling up from these places:
A reminder that the last page of this guide has a downloadable cheatsheet that handily recaps everything you're about to learn.
People think you need to be inspired to write. No, you write in order to get inspired.
As you're writing, how do you know which thoughts are most valuable? What separates good ideas from bad ones?
My approach is to focus on ideas that are interesting or surprising. These are the ingredients of novelty. Novelty is what keeps readers reading. They tend to be:
To uncover interesting ideas, continuously make your next point whatever interests you most. Skip everything that bores you.
When something bores you, it probably bores your readers too. And if something entertains you, it probably entertains them too. You're a proxy for your die-hard readers.
That’s the irony of self-indulgent writing: writing for yourself is the quickest path to writing something others love.
The mistake writers make is believing expertise is required to write compelling nonfiction. Nope, it's the rabid desire to indulge your curiosity.
I just write what I want. I write what amuses me. It’s totally for myself. I never in my wildest dreams expected this popularity.
In addition to interesting talking points, you're also looking for surprising ideas.
Surprise is anything that contradicts what readers know or expect you to say. It makes them think, “Wow. That’s unexpected.”
You generate surprising talking points using essayist Paul Graham’s method: First, learn the basic knowledge of a topic. Then, if you can find new information that surprises your knowledgeable self, it’ll surprise laypeople too. You can also play detective: when you know enough about a topic to know what's not known about it, you can selectively resolve those gaps and share the discoveries.
Again, you are your audience's proxy. There's no need to guess what will surprise them. Hunt for something that surprises you, and others will be along for the ride.
When ideas stop flowing, ask yourself:
Repeatedly ask these two questions and keep moving in whichever direction interests you most.
Your outline should be specific enough to provide structure, but loose enough to not confine expansive thinking. Whenever you feel a tug pulling you away from your outline, indulge that curiosity. Pursue that adventure.
You can prune the bad stuff later.
I hated English in high school. But if they called it Thinking, then I wouldn't be as terrible of a writer as I am today.